Trifluoroacetic anhydride → N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1851548노트

반응식

HRID 1851548 반응식
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([NH2:21])=O)=[CH:15][N:16]=1)=[CH:8]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([CH2:18][CH2:17][C:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])=[N:16][CH:15]=1)#[N:21]

참가 물질

4

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 57901592HCID 57901592, 화합물

생성물 1

HCID 57901663N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide수율 95%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanamide (1.32 g) and pyridine (15 mL) was added trifluoroacetic anhydride (0.90 mL) at 0° C. over 15 min. The reaction mixture was stirred at room temperature for 2 hr and concentrated. 10% Aqueous citric acid solution was added to the residue. The resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.20 g, yield 95%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). melting point 207-208° C.

후처리

  1. concentrationconcentrated
  2. addition10% Aqueous citric acid solution was added to the residue
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-11ca78c5e3fc4d7a807cc92f6955fd30
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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